You had run into John and his two sons about three years ago. You grew up in the hunting life. You met them when John saved you from a vampire. During your time with the Winchesters, things felt semi-normal. Well normal as normal can get for hunters. What you didn't expect was the slowly growing affections for John. True you were twenty-five and john was forty-nine at the time but you couldn't deny he was very attractive. He had the usual rugged hunter look but it worked for him. He had short, dark wavy hair and brown eyes that were both filled with tiredness and sadness. You could understand why.
You had heard what happened to his wife Mary and you could tell how much it still hurt him. He was talking to the boys about finding the thing that killed her. Everything was going as smoothly as it does for hunters until the day Sam announced he was leaving the hunting life for college. You and Dean watched as John and Sam had a shouting match. Both trying to get their point across. "You walk away now boy don't you ever come back!" John challenged Sam. Sam stared at him for a moment and like that he left. Later that night Dean was off drinking. Usually what he did to numb his pain and anger and John was in his motel room. You decided to go check on him.
First, you grabbed a bottle of whiskey and two small glasses and headed to his room. You tapped on the door and a few seconds later John answered. "I just wanted to check on you,". you said. He gave you a small, sad smile and let you in. You poured a glass and held it out to him as you sat beside him on the bed. He chuckled a little and took it and downed it fast. "Are you ok?" you asked.
"I've tried my best with my boys," he said staring into the empty glass, "I know I haven't been the best parent and maybe not the kindest at times but I've tried,". You just nodded and softly patted his back. He looked at you and before either of you knew what happened his lips were on yours. You didn't fight it. You welcomed it. Before long the kiss turned heated. You pushed him down on his back as you straddled him never breaking the kiss as his hands explored under your t-shirt. John broke the kiss to pull it over your head and in one quick motion flipped over until you were on your back. His lips found their way to your neck as you wrapped your legs around him. He trailed kisses from your neck down to your chest as your hands traveled to the zipper of his jeans. It was the best night you had ever had. You hoped so hard that it wouldn't be just a one time fling.